The overall objective of this project is to develop a Diels Alder route to Adriamycinone and structurally related substances. This development includes studies of the effect of remote functional groups on the regiochemistry of the Diels Alder reaction. We also hope to develop general routes to substituted 1,4 dialkoxybutadienes. The current year's objectives are to complete the studies of the regiochemistry of various dichlorojuglone derivatives. We also hope to complete the development of a general synthesis of various 1,4 dialkoxybutadienes, particularly those derived from fused cyclobutene derivatives. Finally, it is expected that we will be able to test the reactivity of these fused bicyclic derivatives to produce derivatives and analogs of adriamycinone.